Monoazo dyestuffs derived from naphthylamine carboxylic acids



Patented Feb. 19, 1929.

UNITED STATES PATENT OFFICE.

LEOPOLDLASKA AND FRITZ WERE R, OF OFFENZBACHON THE- MAIN, GERMANY, AS- SIGNORS TO GBASSELLI DYEST'UFF CORPORATION, OF NEW YORK, N.' Y., A COR- PORATION OF DELAWARE.

MONOAZO DYESTUFFS DERIVED FROM NAPHTHYLAMINE CARBOXYLIC ACIDS.

No Drawing. Application filed May a, 1920, Serial No. 106,547, and in Germany May a, 1925.

This invention relates to new mono-azodyestufi's which contain as one constituent a naphthylamincarboxylic acid and which are suitable for dyeing acetate silk. They may be obtained either by combining a diazotized naphthylamincarboxylic acid with a desired coupling-component or by combining the desired diazo'con'ipound with a naphthylamincarboxylic acid. I

r In the dry state the new dyestulfs are yellow, red, blue to blacki'shpowders which on reduction with stannous chloride yield again the original diazo and coupling components, the latter containing an additional amino group. They dye acetate silk strong yellow,

red to blue-violet shades.

All naphthylamincarboxylic acids and their derivatives may be used as the naphthylamincarboxylic acid com onents. Especially useful are the dyestu s in which the 2.3-naphthylamincarboxylic acid is used and most prominent arethe dyestuffs in which 2.3-naphthylamincarboxylic acid is the coupling component.

Ezmmple I..187' parts of 2.3-naphthylamincarboxylic acid are dissolved hot in 285 parts of 20 B. hydrochloric acid and 1500 parts of water. This solution is then cooled by the addition of ice and treated with an aqueous solution 015.69 parts of sodlum n1- trite. This read diazo solution is added to a solution 'whic consists of'110 parts of resorcin .159 parts of soda and 1000 parts of water. en couplin is complete, the dyestufi having the proba 1e formula:

2.6 naphthylsoda. The carboXylic acid is again precipitated from this solution with 285 parts of 20 B. hydrochloric acid and treated in the cold with an'aqueous solution of 69 parts of sodium nitrite. The prepared diazo solution is added to a solution which consists of 144 parts of beta-naphthol, 159 partsof soda, 40 parts of caustic soda and 1000 parts of water. When coupling is complete, the dyestufi' having the probable formula:

110 nooc is salted out, pressed and dried. It dyes acetate silk a yellowish rosa.

Ewample lll.168. parts of para-nitroortho-anisidin are diazotized in the presence of 285 parts of 20 B. hydrochloric acid by treating with an aqueous solution of 69 parts of sodium nitrite. A hydrochloric acid solution of 187 parts of 2.3-aminonaphthoic acid is allowed to run into this diazo solution and the coupling is finished by neutralizing the excess hydrochloric acid with sodium acetate. The dyestufl' is then treated With 212 parts of soda and then salted out, pressed and dried. It has the constitution: 4-nitro-6- methoxyphenyl azo 2 n aphthylaniin 3-carboxylic acid having the probable formula:

CH O

In the following table several examples dyestufi itself as well as the dyestufis which still contain a free amino group may be further diazotized on the fiber and devehPed with meet the K ein: doihfionents. i g Q a v Color- Diamompound ol'-- Coupled witha I I I of thofld ed. olthedyestufl. 1 meta 2.3-na hth lamin-carbo 11c acid Reddlsh-brown Orange. I p y xy Red.- Red.

Red Rosa. fl-naphthylamlne Red- Brown. v Ethyl-B-naphthylamine Red Red. I l-amino-Mtho'xynaphthaleneo-carboxylic acid fl-m hthm I Green-blue-.. Rubin.

2.6-naphthylaminearboxylic acid Dimethyl-m-tolnldin od.-- Reddish-yellow,

Phenylmethylipyrazolonnn Yellow Yellow. I mphenylene iamin Brow Reddlsh -yellom. w

mtoluylene diamine Yellow-mi.-- Orange. 1.5-naphthylene diemlne Dark brown Reddiah-rubin. B-naphthol s---- Rosa. B-naphthylamine Yellow-orange; Ethyl-B-na hthylamine ,Blulsh-r I w a-uaphthy no) I Orange.

Dlmethylaniline a-naphthylamlne 2.3-naphthylamincarboxyllc acid Yellow-ted o-anhzidln Orange p-aminoacotanllide Orange. p-phanylene diamine ,Brown. p-nitranillne Yellow-whim p-nltro-o-anisidin Darkred-brownnufi Red-violet.

esldine Red Orange 4-dlnltranllin I y Blueblack Bluls violet o-onisidin ao-nnphthylamin'carboxylio acid Roddlsh-yellow Yellow.- aminohydroquinono-dlmethylether a I y ride regenerate the original diazoand conpling-components, the later containing an additional amino group, which dyestufls dye acetate silk in strong yellow, red to blueviolet shades. v

2. Acetate silk material dyed with the dyestufi' as claimed in claim 1.

3. As new com ounds, mono-azodyestufl's which are suitab e for dyeing acetate silk, which dyestufis contain 2.3-naphthy'lamincarboxylic acid as one of the components, which are when dr yellow, red, blue to blackish powders, w ich on reduction with stannous chloride regenerate the original diazoand con ling components, the latter containingan a ditional amino group, which dyestuffs dye acetate silk in strong yellow, red to blue-violet shades.

4. Acetate silk material dyed with the dyestufi as claimed in claim 3.

which .are suitable for dyeing acetate silk,

which dyestuffs contain as the couplingcomponent 2.3-naphthylamincarboxylic acid, I

which when, dry are yellow, red, blue to blackish powders, which on reduction with, stannous chloride regenerate the original diazo-compound and 1.2-(liaminonaphthalene-3-carboxylic acid, which dyestutl's dye. acetate silk in strong yellow, red to blueviolet shades.

6. Acetate silk material dyed with the dye- 40 stuff as claimed in claim 5.

7. As new compounds, the mono-azodyestuff: 4: nitro-G-methoxyphenyLazo-2-na hthylamin-3-carboxylic acid, whichis suita 1e for dyeing acetate silk, which when dry, is a dark red'brown powder, which on'reduction with stannous chloride yields 4t-amino-2- anisidin and- 1.2-diminonaphthalene-3-carboxylic acid and which dyes acetate silk in strong red-violet shades; j v

8. Acetate silk material dyed with-the dyestufl. as claimed in claim 7. I

In testimony whereof, we afiix-our signatures. LEOPOLD LASKA. FRITZ WEBER. 

